


Extra Hours

by winecatsandpizza



Series: Office Matters [1]
Category: Supernatural
Genre: Alternate Universe - Office, Anal, Anal Sex, Boss/Employee Relationship, Creampie, F/M, NSFW, Office AU, Office Blow Jobs, Office Sex, PORN gifs, Porn, Smut, Spanking, nsfw gifs, unprotected sex
Language: English
Status: Completed
Published: 2018-11-24
Updated: 2018-11-24
Packaged: 2019-08-28 16:29:02
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,782
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16726899
Author URL: https://archiveofourown.org/users/winecatsandpizza/pseuds/winecatsandpizza
Summary: Jessy takes a new job as a personal assistant.  Her boss is Dean Winchester.  Jessy wants to make a good impression and will do anything to keep her job.





	Extra Hours

**Author's Note:**

> This was originally posted to my Tumblr here: https://winecatsandpizza.tumblr.com/post/174582687208/extra-hours

 

Jessy had received the call a few days before from the hiring agency.  She was excited to get the call and start a new job.  She was done working in a call center and talking to condescending assholes all day about something as inconsequential as window treatments.  

After she accepted her new position, she was emailed more information about what to expect, job duties, and other pertinent information about the position.  A shiver of excitement ran through her as she kept reading one particular part of the email.

**_Dress Code  
_ ** _The office has a strict business professional attire and must be followed while on office property._

__**Acceptable Attire for Men:  
** Tailored suit (black, navy, gray) with necktie (red, black, blue, gray-solid only. No bowties).  
Black or grey dress shoes.  
White button up dress shirt.  
Hair kept short.  
Minimal facial hair.

 __ **Acceptable Attire for Women:  
** Pencil skirts (black, navy, gray) with matching jacket  
White button up dress blouse  
Stockings or pantyhose (black or nude)  
High heels (minimum of two inches-black or navy. No flats or boots)  
Hair must be in a neat bun or worn down and styled  
Makeup must be professional.

Jessy enjoyed the thought of dressing up for work.  Men in a nice suit always turned her on.  She might have to go shopping to get a few new items for her wardrobe, but she didn’t mind going shopping.

She woke up early for her first day at Sandover Bridge & Iron Inc. She rolled out of bed and headed to the shower.  She welcomed the hot water cascading over her milky skin and raven hair.  After she thoroughly cleaned herself, she toweled herself off and started to get herself ready.

She chose her black, knee-length pencil skirt, white button up blouse, and black suit jacket.  She usually wore this outfit to interviews.  Jessy decided to wear a matching set of lingerie.  They were black and lacey.  She loved the feeling of the lace on her sensitive nipples and clit.  She sat on her bed as she rolled up the black stockings up her legs.  They were thigh high and had lace at the top.  She decided to add a black garter belt to help hold them up.  She slipped on her black heels.  She went to her vanity and did her hair and makeup.

Once she was done, she took one last look in the mirror as she headed to the kitchen.  She filled up her to go mug with coffee and ate a quick breakfast before heading out the door.

The drive to Jessy’s new workplace went quickly with traffic being rather light at this time of day.  She parked her car and walked up to the building.  She stopped and admired the size and the golden letters on the front.  With a smile, she walked through the doors and headed to the elevator.

She pressed the button and waited for the doors to open.  When they did, she stepped out and walked to the office.

Jessy was early, not wanting to be late on her first day.  She was surprised when she already heard a voice talking in an office.  The door was partially closed.  Jessy lightly knocked twice and a manly voice invited her in.  As she rounded the door, she gasped at the man sitting behind the desk.

 

Jessy was instantly drawn to the man’s alluring green eyes.  The depth of them almost made her heart stop.  Even though he was sitting down, she could tell he was tall and well built.  Jessy could make out the muscles of his arms even under the clothes.

“Good morning.  You’re early.  I like that in a woman.  Especially a woman who, from the looks of it, is going to be my new personal assistant,” he announced as he stood up from his desk and came around it, walking towards Jessy.  He held out his hand and pleasantly introduced himself, “My name is Dean Winchester.  I am the Director of Sales and Marketing.  I am also your new boss.”  

Jessy reached out and shook his hand.  His touch sent a firebolt to her core and it took every bit of strength she had in her to keep her composure.  “Hello, Sir.  I’m Jessy.  I’m very excited to take this position under you.”  

Jessy’s face went red with embarrassment as she realized what she said.  Dean licked his bottom lip and smirked and Jessy tried to backtrack, “Oh! No, I’m so sorry. I…I didn’t mean…What I meant to say was that I am excited about my job as your personal assistant and it is an honor to work with you.”

“Well, I’m happy to hear that you are eager to start.  Your desk is right outside my office.  There is a list of your login information sitting on your desk along with a list of things that I need you to get started on.  If you have any questions, send me an email.  Oh, and Jessy?”

“Yes, Mr. Winchester?”

“I have a three strikes rule.  You mess up three times, no matter how small or large those are and your ass is fired.”

Jessy stood shocked and nervous with this new information.

“If you don’t want to have your first strike happen right now, I might suggest that you leave my office and get started,” Dean warned.

“Oh, yes.  Of course, Sir.  Right away!” Jessy exclaimed as she turned around and headed to her desk.

Sitting down in her chair, Jessy took a few minutes to compose herself.  

Jessy tried to give herself an internal pep talk.   _Okay, so my boss is devastatingly handsome and I’ve already managed to admit that I want to fuck him in less than five minutes of starting.  Nothing can go wrong, right?  Come on, Jessy.  Stop thinking of fucking your new boss and start working.  You can’t lose this job._

With that, she logged into her computer and started banging through the items on her to do list.  She was finishing up setting up a meeting for Dean when he came strolling out of his office.  
“You know you  _do_  get to take a lunch, right?” he questioned.

“Yes, of course, Mr. Winchester, but it’s only….” She stopped herself as she looked at the time on her computer which said 1:32.  “Oh, I lost track of time.  I was so busy…”

Dean cut her off, “Listen, Jessy,” his voice softened as he continued, “This job isn’t really that hard.  I’m sorry if I came off a little intense in my office earlier.  Truth is, I go through a lot of assistants.  They either are too old to know how to use a computer, or too young to actually care about the position.  I can tell that you’re different and I don’t want to lose you.”

Jessy felt her heart stop for a moment before he continued, “I know you want this position and your resume absolutely killed it.  You’re going to do fine, but not if you overwork yourself,” he said with a smile.  “Hey, I was about to go head out for lunch.  Come with me, my treat,” he winked.

She smiled, “That sounds wonderful, but are you sure that’s okay?”

“It’s just lunch.  It’s not like I’m bending you over my desk and railing you,” he smirked as Jessy blushed at the thought and felt herself dampen at the thought.  

***

Jessy and Dean had been flirting constantly in the six months that she had been there.  They had grown close and were on friendly terms.  That was, at least, until the two fuck ups.  A few weeks in, Jessy had accidentally shredded a folder of a tax information.  A two months later, she had forgotten to give Dean a message from a client that lost the company new business.

Jessy had been extra careful and took her time to ensure that she did nothing else wrong.  She kept a mental note of the three strike rule in her head and knew she could not mess up again.  Jessy jumped as the phone rang and she saw Mr. Winchester’s extension. He never called her.  Jessy answered the phone happily, “Hi, Mr. Winchester.  What can I-”

“In my office. Now.”

 _Fuck.  He’s upset.  What did I do? I’ve been so careful. Shit, shit, shit!_  She thought as she stood up and walked into his office.  She could feel her heartbeat in her chest.

“‘Sit,” he instructed like she was a dog.  Jessy said nothing as she sat down in the seat like she was instructed.  
“This is your third strike,” he said plainly.

“Mr. Winchester, what did I do? I have been so careful lately, I-” she started to explain herself as he pointed a finger at her.  “Me? What?  I don’t understand?”

“Your shirt.  It isn’t white,” he sounded more disappointed than upset.  She looked down and he was correct.  It wasn’t white, but a very pale pink.  

“Oh, yes, I thought it was white when I grabbed it this morning, but what does my shirt have to do with my performance?” She was so confused.

“The dress code.  It clearly states white button-up shirt.  We had an issue a few years ago with a client getting upset and misinterpreted the color of a colleague’s shirt, so we made everything universal to ensure that no further clients would turn away from us.  We just so happen to have our biggest and most important client coming today for a meeting.”

Jessy stopped breathing while he was talking.  She couldn’t believe that she was going to get fired over a fucking pink shirt.

Dean leaned forward and almost whispered, “I was going to let this go, but with the clients coming in I don’t have a choice.”

Jessy felt the tears coming as she realized this was the end of the line.

“I’m so sorry, Mr. Winchester.  This job means the world to me.  I love Sandover and you’re an amazing boss. I would do anything for this company,” she started pouring her soul out to try and change his mind.  “Look, the meeting starts at 11:30, right? I can just go home or go to the store and change.  Please, I’ll do anything to keep my position. Please.”

Dean held up a finger to stop her, “Jessy, let me stop you there.  Saying you’ll do anything covers, well, everything.  What did you have in mind, Jessica?”

She swallowed the large lump that had grown in her throat.  She knew what she wanted to do.  At this point, it was the only thing she had available to even remotely let her keep her job.  At this point, she had nothing to lose.  If she was going to get fired, she might as well go out with a bang or get fired trying.

She stood up wordlessly as she slid off her jacket, letting it land on the chair.  With shaking fingertips, she slowly started to undo the buttons of her blouse.  She kept her eyes locked on her boss the entire time.  He sat at his desk watching the show.  She slid the shirt off of her shoulders.  She started to undo her bra, until Dean commanded, “Stop.  Hands on my desk and bend over.”

He slung off his suit jacket and watching Jessy as she positioned herself as she was told.  “I always did like that you took orders so well,” he smirked as he positioned himself behind her.  He licked his bottom lip before biting it she looked back at him.  Jessy arched her back to sit her ass further out for him.

She jumped a little as Dean slid his strong, rough hands up her smooth legs.  He started at her calves and slowly worked his hand up to her inner thighs.  He hiked her skirt up over her behind and bunched it around her waist.

Jessy was already soaking her black, lace panties.  She knew her boss could smell her sweet scent and see the wet spot on her panties.  “Mm-mm-mm!” He moaned as he took in the sight of her round ass and wetness presented to him.

“Before we can talk about you trying to earn your way back onto the payroll, I am going to have to teach you a lesson.  I told you that I didn’t want to lose you and you are going to pay for putting me in the position of letting you go.

“Yes, Mr. Winchester,” she managed to moan out.  She felt herself clench around nothing as he rubbed her ass.  “Please - please, punish me, Sir,” she begged.  Within seconds, she felt the sting of a hand spank on her ass. She moaned she he spanked her other cheek with more force.

“Aren’t you forgetting something, Jessica?” Dean questioned.

“I’m sorry.  Thank you, Sir, may I have another?” She begged wantonly.

“That’s a good girl,” he praised as he smacked her cheek again.

“Thank you, Sir, may I have another?”  The spankings continued as so did the intensity of the impacts and her approach of orgasm.  Dean yanked down her panties before the final spanking.

The impact of his large hand on her tendered, reddened ass broke her and she spasmed and squirted on herself as his hand, still on her ass.  “Fuck, baby.  You’re such a good girl taking your punishment.  I think it is time for you to start trying to get your job back.

Jessy’s head was still swimming with the intensity of her orgasm, but she managed to whisper, “ Yes, Sir, please.  Please fuck me.  Need you.”

Dean was already worked up and ready.  He took off his pants and boxes, letting himself spring free.  He lined himself behind her.

He grabbed a fist full of Jessy’s dark hair as he thrust himself into her wetness.  

“Fuck!” Jessy screamed as he filled her.  She was wet enough to allow him in with ease, but his cock was thicker and longer than she was used to.  He filled her completely.  She welcomed the fullness of her boss inside of her.

“Damn, princess.  You’re such a good girl taking my cock,” Dean grunted out as he pounded into her.  Jessy instinctively clenched around him at his praise. “Oh, sweetheart, fuck.”  He smacked her ass again and Jessy spasmed around his length and screamed his name.

“Dean, please-please!” Jessy pleaded.

“Please what, princess,” he asked, his breath on her ear.  

“Please fuck my ass, Sir?” she whispered breathlessly.

“You think you can take my thick cock in your tight little ass, sweetheart?”  Jessy couldn’t manage to speak, but her moan and spasm on his cock was answer enough for Dean.  She whined at the loss of him inside of her but welcomed the feeling of his hot tongue on her hole.  

He slid his index finger into her, stretching her.  Jessy continued to moan as he worked another finger into her, preparing her.  “Please, Sir. Take my ass,” she pleaded.

“Alright, princess.  So eager for me.”  He withdrew his fingers and grabbed her ass as he positioned the head of himself at her entrance.  He slowly sank into her, easing himself in slowly.  Jessy was tired of the teasing.  She pushed her ass back to force him deeper into her.

“Okay, sweetheart.  I’ll give you what you need.”  Dean placed his right food on the table to allow himself to get deeper inside of her.  

“Thank you, Sir!” Jessy screamed as he drove himself deeper inside of her.  

Dean was getting close and he could feel Jessy near as well.  “I’m gonna-gonna…”

“Yes, cum inside me, Dean!”  With that, he exploded inside of her.  He spilled into her with warm ropes as she came with him.  Their breathing was still ragged as he slipped out of her.  Jessy could feel his spendings leaking out of her.  Dean stumbled back finding a chair and relaxing into it.  “Fuck, princess.  So amazin’,” he praised.

“So, did I earn my job back, Sir?” Jessy asked while getting off of his desk.  Her legs were like jelly as she slowly walked towards him in the chair.

Dean smiled, “I think so, baby girl.  You might need to start putting in some extra hours here in the office, though.”  Jessy climbed onto Dean’s lap and straddled him while leaning in for a kiss.

“I think I can manage that, Sir,” Jessy said with a sly smile.  She felt him start to harden under folds.

Dean brought Jessy in for another kiss. “I have some extra white shirts in my closet. Get yourself changed and straightened up.  I want nothing more than to go again, but we have that meeting to get to.”

“Absolutely, Mr. Winchester.”.


End file.
